I've had, I think it was FedEx, where we didn't get money back, and it took months, because eventually the tracking showed up as delivered. We didn't sit there and check tracking but I guess the insurance company did. It sucked because we lost our authorization on the card and when we'd call people up sometimes they didn't want to pay. We didn't store card #s so we couldn't re-bill it and we'd just have to eat it. That really hurt, there were months where we needed every penny, not saying Apple is like this but still, it's really the principle.
Sometimes other people who called up and told us it came after they told us it didn't (where usually we re-sent the order) and we'd just call them and let them know. Then we had to pay for return shipping to get one of the items back. I'm sure some people got through the cracks like the OP here, I guess seeing it from an ecommerce point of view, I hope he just calls and at least tries to do the right thing.
Claims for us usually took 1 - 3 months I'd guesstimate to come to a resolution. I'm sure Apple has a way different kind of agreement and stuff, but I guess as an honest person who has seen the retailer side of it all, I agree with you, I hope he calls.
We are talking about apple. They as are most large companies insured for this stuff. Its a totally different process and believe me that they don't what the product back.